Today’s post is the latest installment of our Q&A Series – short interviews with talented, experienced, and successful entrepreneurs who are on the front lines of running online businesses.

My guest is Michael W. Kearns, CEO of TurnkeySchool.com – a school CMS website that Mike and his business partner  Jake Johnson developed.

I think you’ll like this discussion. Michael shares some great insights.

Here’s our discussion:

Today’s post is the latest installment of our Q&A Series – short interviews with talented, experienced, and successful entrepreneurs who are on the front lines of running online businesses.

My guest is Reed Humphrey. Reed’s an experienced entrepreneur having cofounded or led marketing at four start-ups, including a tax services firm that grew revenue by 100-fold under his direction. Currently he leads the marketing and public relations functions for New River Innovation/easyIRS.com, including advertising, social media, partnerships, news and media.

I think you’ll like this discussion because Reed is a smart, experienced guy who is right smack dab in the middle of the startup experience. He’s got a lot of good input on financing and marketing. And his company is working on a pretty cool idea that I think could be huge.

Here’s our discussion:

B5: The name of your company, easyIRS.com, probably says everything. But just in case, tell me about what the company is all about.
Reed: easyIRS.com is focused on solving personal IRS concerns beyond April 15 by automating tax analysis and support. Examples of IRS concerns include tax debt, unfiled tax returns, audits, liens, levies, and penalty abatements.

Our vision is to create the world’s first web service for IRS problem resolution. We are similar to WebMD or LegalZoom, except with a dedicated focus on tax problems. It’s all about eliminating the fear and uncertainty of dealing with the IRS, and providing people with practical solutions.

B5: Can you give me some idea of the scope of this market? How many people struggle with IRS and tax related issues?
Reed: The target market for easyIRS.com is approximately 32 to 35 million taxpayers whom the IRS contacts every year (about matters ranging from simple math errors to delinquent tax debt). The market is served by CPAs, tax attorneys, enrolled agents and tax resolution firms such as JK Harris, Tax Masters, and Roni Deutch.

In recent weeks, we’ve seen a big momentum shift concerning those “pennies on the dollar” tax debt resolution firms. New FTC legislation prohibits debt relief firms from charging upfront fees or making false promises about debt reduction, and requires them to adhere to strict disclosure standards. The rule’s implications for deceptive tax debt resolution firms are catastrophic, because many of the firms depend on charging large upfront fees.

We’re glad to see the industry cleaned up and consumers protected. And we’ve invested millions of dollars in automating IRS response systems, so that consumers can solve their own tax issues, without paying big fees to tax relief firms.

B5: What makes EasyIRS.com qualified to help taxpayers with their issues?
Reed: We are staffed by a team of IRS and tax experts, including a CPA, enrolled agents, tax preparers, IRS negotiation case managers and certified tax professionals. This team has more than 100 years of combined experience working with IRS, accounting and tax-related issues. They apply this knowledge and experience in solving personal tax concerns beyond April 15 by automating tax analysis and support. These tax and accounting experts are complemented by technology professionals experienced in high-security applications.

B5: How’s it going so far?
Reed: It’s going great! We’ve been busy developing our solution set for the past few months. We are preparing for a national launch of easyIRS on Dec. 1 (just ahead of tax season). Our value proposition is “The best way to solve your tax problem. Save money. Fix your tax situation. Guaranteed.”

Because we are an online software provider, easy IRS fees are 95% lower than traditional tax resolution firms. We do not make unrealistic promises of debt reduction, and all of our services are backed by a 100% Money Back Guarantee. No other company is doing what we’re doing, and we think this changes everything in our industry.

B5: What advice can you share with readers about having the right financing partner(s) for an early stage company?
Reed: I can’t emphasize enough the importance of finding the right financing partner. I have been a part of four start-ups, with financing provided from founders, banks, angel networks and venture capital firms.

I can honestly say that our relationship with Intersouth Partners has been the best. Intersouth took a risk on us as a seed company at the zenith of the economic downturn in mid 2009. They saw something in us that others did not. Our sponsors, Mitch Mumma and Katrin Burt, meet with us every month for 2 to 3 hours, and they provide business insight and experience that are priceless. They understand our business, and they bring so much more than just capital to the table.

B5: Let’s jump from financing to marketing. What is your content strategy? (How are you getting traffic to your website?)
Reed: We’re committed to providing the most authoritative, complete database of IRS tax debt information on the web. Statistics from 2009 show that the IRS sent more than 200 million notices to American taxpayers, more than 26.4 million IRS penalties were assessed, 3.5 million taxpayers broke a payment agreement, and close to 69 million audits were conducted. With all this activity, it is clear that there is a tremendous need for easy-to-understand content. We’re committed to providing expert content through a variety of channels; we have hundreds of articles, videos, and slideshows related to various tax topics, all of which are available on our website.

EasyIRS has created the nation’s first taxpayer advocacy site, specifically focused on IRS problem and resolution topics. The “Learn” section of our site is free, and it features hundreds of original stories, videos, slideshows, and how-to articles designed to simplify dealings with the IRS. We’re organizing and optimizing this site for SEO purposes, and we believe that free leads and word of mouth will be huge drivers of traffic, as will PR and social media.

B5: What’s your split between organic versus PPC?
Reed: We have been using PPC to test, but many of the keywords are expensive relative to our low price point. PPC makes sense for tax-resolution service firms that charge upward of $3,000 for their services. This is not true for easyIRS.com, because we charge less than $150 per engagement. So, content, social media, public relations and search engine optimization (SEO) are clearly our best long-term plays.

B5: What tips can you share with our readers about traffic acquisition?
Reed: Inbound lead generation, Sales 2.0, and content generation are the wave of the future. Traditional mass media channels will continue to be less effective until the day when they start sharing the risks and rewards with advertisers. By that, I mean that offline media needs to stop charging exorbitant fixed fees and start offering more tracking, reporting and ROI accountability. So, start your marketing with low-cost, measurable, online sources. Explore all avenues there before you consider dumping cash into a big offline media buy.

B5: What can we expect to see from easyIRS over the next few months?
Reed: Over the next 12 months, we expect our company to reach $3 million to $5 million in revenue with 40 employees (currently 20). Within 5 years, we hope to establish easyIRS.com as a household name, the first site anyone would visit if he or she had a problem with the IRS.

What are you thoughts on all of this? Got any reactions? Let’s discuss in the comment section below.

Here’s the latest installment of our Q&A Series – short interviews with talented, experienced, and successful entrepreneurs who are on the front lines of running online businesses.

My guest is Curt Dalton, founder of the new search engine NowRelevant.com – yeah that’s right. I said new search engine. I had a chance to chat with Curt this week. He had a lot of great insight’s about the entrepreneurial game and the search business. He’s got an interesting idea.

This interview is super interesting because of the industry involved – one that’s obviously occupied by giants that we’ve all heard of. Here’s our discussion:

B5: Before we get into your new venture, tell me about being an entrepreneur.
For me it has always been about how you think about a problem and how you look to solve it.  I have always been the “I can create a better mouse trap” type thinker.  So, you will strike out some, but you if you stick with it and be persistent you will find success on a project sooner or later.

B5: So tell me about NowRelevant.com.
NowRelevant.com is a new search engine that shows you everything about a subject, but just for the last two weeks. We want to give users relevant information on topics without having to sift through 55 million results that date back to the beginning of time. We’re able to remove spam and SEO dummy sites from the users results as well.

B5: My first reaction is that there are some big players in search. What made you decide to get involved?
Well, NowRelevant.com was our own search engine that we had to build in order to run The Internet Time Machine trend analytics software – one of my other ventures. We realized that over the past 8 years of creating the Time Machine, that we also built a very powerful and new search engine. We are able to get blogs and forums indexed and to the user much quicker than Google can. So we felt like we were on to something.

B5: How do you make money?
NowRelevant.com offers a robust platform for advertisers such as the use of video in PPC ads and a 20 percent commission to affiliates on our pay-per-click (PPC) program.

B5: What’s the profile of your target user?
We see the Twitter-Facebook generation as our ideal user – a user that has tons of information thrown at them everyday but wants just updated, non-spam based results.  They aren’t looking for an historical perspective on the subject of their search, just very recent and current information on the subject.

B5: Is NowRelevant.com backed by any investors, or is it bootstrapped?
As of right now it is a big pair of army boots.  No complaints. We have never tried to raise money yet.

B5:A lot of our readers face the dilemma of how to properly fund their ventures. Can you talk about why you took the company in that direction?
Equity is the most important thing you have in your company, and you should only give it up when it makes tons of sense or you need to do it to survive.  Based on past success we haven’t need to do that with NowRelevant.com or TheInternetTimeMachine.com.  I understand a lot of people don’t have money just laying around to fund their own startup, so the have to give away equity in order to get the ball rolling. But my advice would be: don’t do it if you don’t have to.  Once you introduce shareholders or equity holders, life gets complicated and you have someone you need to report to and explain yourself to.

B5: Back to the business….what, specifically, makes you different from the big dogs in search?
With the historical clutter that frankly overwhelms the web (not all of the html pages are clutter, but much of it is irrelevant content) we wanted to set up a complex system of filtering and algorithms to give you just discussions and information about your subject for the past 14 days only.

Contemporary search engines have all been presenting us with most recent ‘additions’ to the web database, and have concerned themselves with making the most valuable of these new daily additions available to the public on a minute by minute, day to day basis. Search Engines are therefore able to run pay-per-click engines on top of their search interfaces. The advertising media is based purely on keywords input by users at the time of the search, and users of PPC advertising services on search engines have become a target for massive levels of spending incurred as a result of there being a serious lack of a ‘targeted’ and more ‘focused’ PPC engine that allows users to maximize on their PPC exposure by choosing keywords that they know are in demand, or have received considerable mention on the internet.

We allow users of our PPC campaigns to access the wealth of its resources dating back chronologically to exactly 14 days from the time of their search. This enables both the viewers of search results as well as PPC advertisers to target their PPC campaigns to a specific set of keyword phrases that are bound to receive public attention no matter what, enabling advertisers to compete better on NowRelevant.com with a much lower advertiser competition ratio than found on any other search engine.

Users of our search facilities will be able to retrieve a specific subset of information dating back on 14 days, allowing them to immediately benefit from the most up to date and recently mentioned information. Users of the our PPC engine will therefore be able to reap the benefits of a highly focused PPC campaign where advertiser competition for a specific set of keywords changes by the minute – it’s based on the most recent information coming into our databases by the minute, so there’s no chance of the same CPC levels staying for more than a minute either!

B5: Let’s move on to marketing. This is a really unique situation since I’m guessing you’re probably not going to market on Google. How are you going to get users?
I believe for a search engine to make it a group of people have to own it, as in put it into their personality, as in “I use NowRelevant.com because I am relevant and in the moment”.  So we are doing viral videos, and blog posts about it in order to promote a social trust and word-of-mouth feel. You can’t just put banners up and say “go use us”.

People like to buy something, not be sold something.  That is a big distinction.  If somone finds NowRelevant.com from a video or blog, then they can pass it along to their friends as a new and exciting thing, as opposed to seeing a banner and having it shoved in their face.

B5: What tips can you share with our readers about traffic acquisition?
Well, great question. That’s the golden goose right there. You can have the most life-altering product ever created, but without traffic, you are dead. There is no magic bullet.

I believe in a two-pronged approach: do your testing with PPC to get traffic started and see how things convert. But also put time and money into your long term link-building and viral markets.

Much like life, marketing isn’t 100% this, or 100% that. You need to do a little of this, a little of that. Give it time. Build up creditiblity slowly. The Internet is craving authority figures and sites. As the amount of pages on the Internet doubles every 9 months, everyone needs an authority figure in a niche to tell them which product or idea to follow since there is too much information out there for one person to follow.

B5: How much of this entrepreneurial life that we live is skill versus luck?
You create your own luck by working at it everyday and not giving up.  Everyday you need to do something productive for your business. Adding links in blog comments, starting forum conversations, starting an ad campaign. Whatever. Just do something positive to grow your business everyday and those little increments will add up to a lot over a year or two. Lucky breaks, as they are called, often happen because you have been working everyday on something and then finally caught someone’s attention or Google noticed you.

B5: What are NowRelevant.com’s plans for the future?
We hope to increase our spiders so we can pull from more sources as we grow. We think there is huge demand for non-corporate based results that Google is stuck showing due its size and corporate relationships. Adding spiders for different languages would be big as well.
Thanks again to Curt for sharing his thoughts.

Got any reactions? What do you think about Curt’s take on search? Let’s discuss in the comment section below.

This the latest installment of our Q&A Series – short interviews with talented, experienced, and successful entrepreneurs who are on the front lines of running online businesses. I’ve always believed that it’s a big mistake to not at least listen to those who have worn the same shoes that we are putting on every day. I hope these interviews prove to be as informative to you as they have been for me.

Today’s guest is Wray Rives, founder of NeedaCFO. I had a chance to chat with Wray recently. He had a lot of great insight’s about year one of his newest venture.

Here’s our discussion:

B5: Talk a little bit about what NeedaCFO is all about.
WR: For several years I have worked with medium-to-large companies providing C-Level management support, mostly in the financial (CFO/COO/Controller) type roles.  At the same time, I have had a few fairly small business clients that I mostly do tax compliance work for.  I saw the need with the small business owners to have a senior level business advisor like a CFO or COO, but most of them cannot afford a full time person. Even if they have in-house accounting and finance staff, many small business owners end up performing the CFO role themselves, because the in-house staff is focused on day to day accounting duties and is not really looking at the business in a “big picture” way.

In my experience, small business owners tend to fall into two groups a) really good at some technical skill or b) really good sales people.  Very few of them are really good CFO’s. I felt like they needed somewhere to go and get solid business advice.

B5: How do you make money?
WR: I charge a set fee or hourly rate for services provided.

B5: How long has NeedaCFO been in business? And how long have you been associated with it?
WR: NeedaCFO has been in existence for about a year, and I have been involved from day one.

B5: Is this your first entrepreneurial venture? If not, what else have you worked on?
WR: No, I have been a partner in or owner of public accounting practices since 1993.

B5: Talk a little bit about your desire to be an entrepreneur. Is it something you’ve always had? Or did it happen all of a sudden?
WR: I think I have always had the desire to be an entrepreneur.  I tend to be very results oriented and become impatient when I have to deal with people who throw up roadblocks to moving forward.  I guess you would say I am a “get on the bus or get out of the way” type person.

B5: Tell us about the most valuable learning experience(s) you’ve had with the business.
WR: I learned that I have to adapt to what the market is telling me and not solely focus on my personal vision for the business.  NeedaCFO has expanded my own brand and early on I started getting inbound requests about doing tax work.  Although I do tax compliance work as a CPA, at first I was resistant because doing tax returns was not what I had envisioned for NeedaCFO.  I guess the lesson is you need to be true to your vision, but also be adaptable and willing to listen to what the marketplace tells you it needs.

B5: Is NeedaCFO backed by any investors, or is it bootstrapped?
WR: It is totally bootstrapped by me.  The nature of the business is that there have been several peaks and valleys with revenue.  I do think the current economy has helped me because
1)businesses are looking for the services we offer whether they are an established business needing to control costs or startups that just need advice, and
2)there have been plenty of talented finance and accounting people who are unemployed or underemployed and willing to work on a contract basis when I have needed to ramp up and then move to something else if the work trails off.

B5: A lot of our readers face the dilemma of how to properly fund their ventures. Can you talk a little about why you took the company in that direction?
WR: I bootstrapped the venture, because you can’t find funding for a startup whose revenue stream is based on providing a personal service.  Funny thing is if you look to buy an existing service business, you can have people lined up around the block to fund you, because there is a concrete history of cash flow they can point to and get comfortable with the deal, but no one is going to fund a personal service startup.

B5: Knowing what you know now about financing, what advice would you give a new startup trying to figure out the best option to finance their idea?
WR: My advice would be to try and understand the wants and needs of the person providing the financing.  If you can show how your idea is going to meet the needs of the money people, they will be much more willing to work with you, but remember no one is going to be as enamored with your idea as you are.

B5: How much of your marketing strategy is organic search versus PPC?
WR: Almost all of my strategy is organic.  When I started out I tried a lot of PPC options, but I kept getting more response from the organic efforts.

B5: What can you tell us about your strategy for each?
WR: I think if you have something concrete that people want to buy, PPC can be very effective because you just need them to find out where to get your widget.  But if you are selling a service, people are looking at whose behind the service and PPC can actually work against you because you risk looking like you are trying too hard. Actually we recently moved our website over to be a Ning network trying to make it more of an interactive experience rather than visitors just getting a marketing spiel from the business.

It takes time and effort to build an online reputation and you have to be willing to show that you can provide value to build trust with people.

B5: What tips can you share with our readers about traffic acquisition? What have you learned that you didn’t know when you started the business?
WR: I try to stick with an 80/20 rule in social media.  80% is providing value and 20% is asking for something in return.

There are folks who are a lot smarter than me about building SEO, and I probably could have saved some time and effort by consulting with them starting out. Luckily I took a shotgun approach in the beginning and it was really not that hard to start identifying things that were working and those that were not, so I could start focusing my efforts where I was getting return.  I also keep listening to those folks who are smarter than me and pick up little nuggets every now and then.

B5: How much of entrepreneurial success is skill versus luck?
WR: I think everyone has skills and entrepreneurial success is about attitude.  With any startup, there are going to be hundreds of times that you are going to question should you be doing this, especially when people you love and respect ask if you should be doing this.  You have to have an attitude of perseverance and willingness to keep pushing ahead.  Plus a healthy dose of luck never hurts.

This the latest installment of our Q&A Series – short interviews with talented, experienced, and successful entrepreneurs who are on the front lines of running online businesses. I’ve always believed that it’s a big mistake to not at least listen to those who have worn the same shoes that we are putting on every day. I hope these interviews prove to be as informative to you as they have been for me.

Today’s guest is Elizabeth Pitt, CEO of CareGiverNeeded.com. I had a chance to sit down with Elizabeth recently. She’s extremely bright and has some really valuable insights on starting a business for the first time, acquiring traffic, and the importance of learning as you grow.

B5: Talk a little bit about what CareGiverNeeded.com is all about.
EP: CaregiverNeeded.com is the fastest and easiest way to find senior in-home care on-line. We have thousands of in-home senior caregivers on our site, and hundreds of in-home care agencies, so when a family is looking for care, we are an ideal resource. We answer a lot of questions families have about home care on the site, and we have experienced caregivers on staff to answer questions live.

B5: How do you make money?
EP: We make money from subscribers who pay to see all the contact information for caregivers, and from home-care agencies who pay to be in front of families who need care. We also make money from Google ads embedded in the content on our site.

B5: How long has CareGiverNeeded.com been in business? And how long have you been associated with it?
EP: The company has been in business since 2005. I’ve owned it since May 2009.

B5: What’s your experience with the company been like so far?
EP: Buying a business has been an amazing and life-changing process.  To go from an employee in a company to a 100% shareholder requires such growth and such a shift in mindset. I had to make that shift quickly, and I am still making it.  I’ve had some tremendous successes, and more than a few surprises. But for 9 months into the business, we’re doing well.

B5: Tell us about the most valuable learning experience(s) you’ve had since taking over the business.
EP: There are quite a few lessons I’ve learned so far, including:

1. Whatever you think you need in cash and time to get the business humming, double it. If you started your own business, you are by nature optimistic. You think that things will go better than planned and cost less than planned.  You are wrong.  New things are uncertain. Your business will eat up more time, money and energy than you could ever think possible.

2. Invest in your education. You just can’t be an effective owner of a business that’s web based until you have a firm grasp on internet technology and search engine basics. Find mentors, seminars, courses, books and educate yourself about SEO/SEM, web technology, your industry, finance/investing, and sales and marketing. You may have learned all this in business school, but take the time to refresh, and do it from the perspective of a small business owner. You will never regret an investment in yourself.

3. Vendors who are selling you things have very different incentives than employees you may have worked with when you had a J-O-B. Make sure the money follows their performance. Pay as little as possible up front, make no progress payments, pay the most at the end, and reserve a little in case they screwed up so that they have an incentive to fix it.  Or, if feasible, set up a small, test project or pay for some hourly consulting to test the waters first.  I don’t mean to be cynical…it’s just that incentives are different in the free market than in the corporate world.

B5: Is CareGiverNeeded.com backed by any investors, or is it bootstrapped? Bootstrapped. Can you talk a little about why you took the company in that direction?
EP: I purchased an existing business to reduce some of the risk – the value proposition has already been proven, and it just needs to be tweaked here and there to grow/become more profitable. I had the financial wherewithal to finance that stage of the business, so it made more sense to keep control/ownership to get started.  We are investing in tests to find growth levers, and if we find a way to make the business really take off (but that will probably suck up cash in the process), it will be an appropriate time to take on an investor. The fiduciary responsibility of outside cash is non-trivial, and I want to take it on when I have a clear picture of how it will benefit the company.

B5: Your company doesn’t offer any physical products or have any physical locations. What’s unique about running an online pureplay?
EP: It can be hard for others to understand your business…bankers/investors, customers, advertisers…because as much as people use the Internet, it can still be hard to grasp Internet business models. Also, you must, as the chief executive of the company, have a deep understanding of all the web levers. This can’t be under-emphasized. Though my business is in senior in-home care, so I have to know as much as possible about that subject and the competitors/partners who offer similar products for the same customer need. When it’s a pure play, knowing as much as possible about the Internet as a sales channel is imperative. You can’t outsource it. It is a huge part of what the business is about.

B5: How much of your marketing strategy is organic search versus PPC?
EP: 100% organic. We are testing PPC campaigns now.

B5: What can you tell us about your strategy for each?
EP: They are complementary strategies.

Before even looking at organic vs. paid, you need to diligently think through your macro search strategy.  To win in any business, you need to solve an important problem or fulfill a need. In the world of search, you must understand what need your product/service meets for customers, and what words they would type into a search bar to get that need met. More specifically, what words are they typing in when they are just doing research vs. when they are ready to pull their credit card out and make a purchase? How do you want to interact with them during their search and buy process?  What words and terms let them know that your product/service is a perfect match for what they are looking for?  Once you do the research to understand that, you need to filter by the territory your competitors may have already staked out. Is there someone who’s already optimized for a lot of the terms you want?  Or are competitors paying an arm and a leg to buy certain terms at prices that could never be profitable for you?  If so, what terms are still good for you, but not already dominated by another player? Or, are there multiple, lower volume terms that you could focus on that competitors aren’t focused on today? The result of this analysis would be your “keyword strategy”, and then you can start to think about organic vs. paid.

I think about organic as the core, bread and butter, what you want to be known for set of keywords, and also the words more aligned when someone is doing research to get them to land on your site so that you can convert them to paying customers downstream with a good user experience. I think of paid as the set of keywords that mean someone is really close to buying, really teed up and ready to go, and you grab them and convert them. I also think of paid as a way to test out a new set of keywords or marketing messages that you think might appeal to customers, but you’re not quite sure. You can get good quick and dirty feedback on an idea/concept/marketing message with paid search.

B5: What tips can you share with our readers about traffic acquisition? What have you learned that you didn’t know when you started the business?
EP: With traffic acquisition, there are the basics, and then there are the new/cutting edge strategies.  You need to have your basics in place before you get creative. You need the right tags, the right indexing in Google, the right page tracking. If you don’t have the basics covered, trying all the buzz-filled techniques of the day are a waste of time.  And the basics can be hard to get completely covered. If you think you’re close, find an mentor/expert/specialty firm in search to give you the once over and help you tweak.  (Finding good help takes a lot of work, by the way) Once your basics are covered, then figure out some of the techniques to give you extra “juice”.  This depends on your business. It might be to focus regionally and have a way to get regional searches to your site. It might be to start a blog, or start publishing video content.  It might be to create “feeder” sites on similar, complementary topics that can get clicks to your site.

B5: What are CareGiverNeeded.com’s plans for the future?
EP: Right now, the business is cash flowing and profitable! The next phase is growth. We are exploring whether we have some good levers to pull for growth that will add value to our customers, that we will deliver and fulfill to the level of their expectations, and with which we can be profitable. But we are keeping our eye on the core business and making sure it runs well before heading off in too many other directions.

This the first installment of our new Q&A Series – short interviews with talented, experienced, and successful entrepreneurs who are on the front lines of running online businesses. I’ve always believed that it’s a big mistake to not at least listen to those who have worn the same shoes that we are putting on every day. I hope these interviews prove to be as informative to you as they have been for me.

Our first guest is Ryan Thompson, co-Founder of FileLater. I recently had a chance to sit down with Ryan. He had some great insights on starting a business, traffic, and the importance of listening to customers.

B5: Briefly, tell me a little about what FileLater is all about.
RT: FileLater was developed to help the 15 million people who file tax extensions every year.  There are a lot of misconceptions around tax extensions, and until FileLater, there wasn’t an easy way to get more time to do your taxes. So, we created one leveraging our expertises on the internet and taxes.

B5: How long has FileLater been in business?
RT: FileLater is 3 years old, although we spent about half of that time researching, building the product, and working with the IRS to become and authorized IRS e-file provider.

B5: I won’t ask you to get into numbers because I know how secretive startups are about sales, but how are things going so far?
RT: Things are going much better than expected, and we’re having a lot of fun doing it. It’s a real satisfaction to know you’re removing so much stress for thousands and thousands of folks by letting them know there’s an easy way to get more time to do their taxes. We’ve really learned to appreciate and listen to what our customers want, and we really believe that’s been instrumental in growing the business as quickly as we have.

B5: Are you backed by any investors, or is FileLater bootstrapped?
RT: Wow – how much time do you have for me to explain this one? The short answer is that we are entirely bootstrapped.  Although, we’re a little lucky it turned out that way. We talked to lots of potential investors along the way and the bank account ran pretty low in Year 1. Looking back, that was good for us. It’s really amazing how creative you can be when needed to save on expenses. Luckily, we’re in a much better position now and can invest in growth.

B5: Your company doesn’t offer any physical products or have any physical locations. What’s unique about running an online pure-play?
RT: I think the most unique thing is that there’s almost an expectation that you don’t support your customers because everything is online, which I think is just the wrong way to do business. Think about it – every restaurant or retail shop you go to, you’re generally greeted by warm smiles and “Thank Yous” on the way out the door. When you’re serving tens of thousands of customers over such a short period of time, it’s much harder to do… but, as I said, that’s very important to us and part of how we see ourselves different than other online tax providers.

B5: I would think qualified traffic is pretty much do-or-die to your business. Is that true?
RT: Yes. The reality is that everyone who buys from us starts as a lead one way or another.  We do see a lot of word of mouth and return users, but still the vast majority come from our marketing efforts. Establishing ourselves in the search space is very important to our success.

B5: How much of your marketing strategy is organic search versus pay-per-click?
RT: Our strategy certainly includes both, but I’d say we spend 70-80% of our search efforts on organic. The decision really comes down to return on investment.  It’s no surprise that bidding on tax related terms in April isn’t cheap, and it’s very competitive. So, we’re better off focusing the majority of our search efforts on SEO, and we’ll compete in PPC where it makes sense. Plus, SEO has a longer term benefit that brings additional value to our company. There are lots of companies out there that get acquired for their SEO rankings alone.

B5: What else can you say to startups about SEO?
RT: Come up with a plan and start executing it early. Once you start, stick to the plan and be patient. We are a very seasonal business. Every year we come up with a 6-month plan for creating new content and getting new links. The trick is sticking to it and not over-reacting if what you are doing doesn’t always result in instant success. Even today we are seeing benefits from some of the things that we did last year. Patience is key.

B5: What tips can you share with our readers about traffic acquisition?
RT: That’s a great question. Well, first I’d say that there are no shortcuts.  Things like link exchanges or black hat SEO tactics just don’t work in the long term. You’re much better off investing in the right content and earning your way to the top of SEO.  Also, having the best product will earn you word of mouth that will really help you grow. And, as hard as it is, you have to have some element of patience. Growing a strong following for anything simply takes time and effort.  Oh, and when someone tells you they have a shortcut and it seems too good to be true, it probably is, and I say all of this from experience.

B5: What have you learned that you didn’t know when you started the business?
RT: Well, as I mentioned earlier, we knew technology and the tax space pretty well when we launched.  However, the Internet changes so quickly that you have no choice but to keep up. Things like social media, advancements in SEO strategies, and new developer tools are moving so quickly that you’ll get left in the dust if you don’t keep up with them.  And, I’d also reiterate the focus on making a great customer experience. We knew it was important when we started, but I don’t think we completely understood the magnitude of what it means to have a product that customers will tell their friends about.

B5: What are FileLater’s plans for the future?
RT: We’re committed to having the best tax extension service on the web. There are other tax and let’s say “civic duties” that we think we can use the Internet to help simplify, but we’re carefully balancing that against finding a niche and solving it very well. Between now and mid-April, we’re heads down with tax extensions, and we’ll regroup when the dust settles to flush out the rest.

What do you think? I’d love to hear your thoughts in the comments section below. Don’t be shy!